Solid diazosalts of ortho-aminophenolarylethers



7 they produce.

Patented July 17, 1928.

UNITED STATES PATENT OFFICE.

IEBDINAND KELLER, 01 OFFENBACH-MLIN-BURGEL, AND SCHNITZSPLH N 01' OFFENBACH-ON-THE-MAIN, GERMANY, ASSIGNORS TO GBASSELLI DYESTUIF COB- POBATION, 0] NEW YORK, N. Y., A CORPORATION OF DELAWARE.

SOLID DIAZOSALTS OF ORTHO-AMINOIHENOLABYLETKEBQ.

No Drawing. Application filed February 11, 1927', Seriallo. 167,581, and in Germanylebruary 12, 1988 This invention relates to new solid diazosalts of the general formula:

O-aryl 51 wherein the Xs stand for hydrogen atoms, of which one or more may be'replaced by a monovalent substituent and aryl represents an unsulfonated arylresidue, which diazosalts may be obtained by double decompositionreaction of mineral acid diazosalt solutions of ortho-aminodiphenylether and its unsulfonated substitution products, obtained in the customary manner and sufiiciently concentrated, either with a ara-chlorobenzene sulfonic metal salt or, wit free para-chlorobenzene sulfonic acid. The new salts separate from their solutions as crystalline whitish to yellowish to brownish colored preci itates and can be easily filtered and dried.

n--U. S. Patent No. 1,629,906 stable diazosalts of ortho-aminophenolar lethers are described, which are. obtained by treating the diazoderivatives of unsulfonated ortho-aminophenol aryland alkarylethers with arylsul onic acids, particularly with monoand polysulfonic acids of the naphthalene series and with nitrobenzene sulfonic acid;

In view of the fact, that the arylsulfonates on the one side and the various diazocompounds on the other side are strongly difierentiated, when reacting with each other, it could not been foreseen, that the para-chlorobenzene sulfonic acid would be suitable'for separating solid diazosalts of ortho-aminohenol arylethers, whereas the very similar enzene sulfonic acid is unfit for this purpose. In fact, however, the new para-chloroenzene sulfonic diazosalts of ortho-aminophenolarylethers are distinguished by the capability of being readily separated and a good stability and the clearness of the shades The new solid diazosalts are valuable diazosalts preparations for dyeing and printing. Under certain conditions it has been found advisable to add to the diazonium salt preparations such substances 1 as are useful 1n dyeing processes.

The following examples-are given to illustrate the invention, the parts beingby weight:

' Example 1.

E'aiample 2.

1 To a filtrated diazosolution, prepared from 110 parts of 4-chloro-2-amino-l-diphenylether, 950 parts of hydrochloric acid (density=1.05) and 185 arts of. a solution, con-'- taining 40% of so ium nitrite, a concentrated aqueous solution of 116 parts of free gara-chloro-benzene sulfonic acid is added.

he separated diazosalt having probably the formula:

is then dried and mixed with 400 parts of the technical sodium salt of 1.6-naphthalene disulfonic acid. The mixture is a brownish and in water soluble powder.

The same good result is obtained when starting from other ortho-aminodiarylethers, substituted in one of the arylresidues or in both. v

We claim: I

1. As new compounds solid diazosalts of ortho-aminophenolarylethers of the general formula: I

O-aryl X wherein the Xs stand for hydrogen atoms, of which one or more may be replaced by chlorine and aryl represents an unsulfonated arylresidue, which diazosalts are whitish to yellowish to brownish colored and soluble powders, being substantially identical with products obtainable by double decomposition reaction of mineral acid' diazosalt solutions of ortho-aminaphcnolarylethers either with a para-chlorobenzene sulfoni'c metal salt or with free para-chlorobenzene sulfonic acid.

2. As new compounds solid diazosalts of ortho-aminophenolarylethers of the general formula: Y

wherein the Xs stand for hydrogen atoms, of which one or more may be replaced by chlorine, which diazosalts are whitish to yellowish to brownish colored and soluble powders being substantially identical with products obtainable by double decomposition reaction of mineral acid diazosalt solutions of ortho-aminophenolarylethers either with a para-chlorobenzene sulfonic metal salt or with free para-chlorobenzene sulfonic acid. As new compounds solid diazosalts of ortho-aminophenolarylethers of the general formula:

wherein X stands for hydrogen or chlorine which diazosalts are whitish to yellowish to brownish colored and soluble powders, be-- ing substantially identical with products obtainable by double decomposition reaction of mineral acid diazosalt solutions of a para-substituted ortho-aminophenolarylether either with a 'ara-chlorobenzene sulfonic metal salt or with free sulfonic acid.

4. As a new compound the solid diazosalt of para-chloro-ortho-aminodiphenylether of the probable formula:

C] being a brownish colored and soluble powder para-chlorobenzene a and being substantially identical with a prod- 

